These questions may be an acquired taste. I quite enjoy interesting conversations. Hopefully, these questions can elicit a story from conversation partner.
Current favorite questions:
What do you regret? What do you not regret?
Suppose you had to (or got to, depending on your perspective) make a binding commitment to do one thing for an hour per day (e.g., âgo runningâ) â what would you commit to?
Who are you most similar to? How are you different from them?
What is an under-cared about large societal problem? (bonus points if I donât currently know/care about it, but you convince me that I should).
What percentile do you/I fall in for âbeing socialâ? for âbeing happyâ, for âbeing niceâ, âconformistâ, etc. Basically, the q is, pick some interesting âcharacterâ dimensions and ask where person falls. Often elicits good stories â e.g., a âproofâ that Iâm âsuper socialâ or Fermi estimations. Good to discuss positive and negative aspects of the characteristic, whichever side of the mean it falls on.
Suppose the world was about to end, or your friend was about to die. Do you have a responsibility to try to stop this?
What are your top priorities?
Talk about AI.
- Tell me about your name.
- Whatâs your favorite thing about yourself?
- Favorite book? Favorite character?
- Do you think people (generally, or you or I) ârise to challengesâ or âcrumple under pressureâ? / do high stakes elicit high performance?
- Whatâs your favorite piece of clothing? / favorite material possession?
- How are you similar and different to your parents?
- Whatâs something youâre worried about?
- Whatâs something good that youâve done lately â by more than 2SDâs?
- What would constitute a âperfectâ day for you?
- For what in your life do you feel most grateful?
- What is something youâre proud of yourself for?
- What in life do you get truly excited about?
- Whatâs one thing you canât live without?
- What are the chapters of your life?
- How does the way you see yourself differ from the way other people see you
- For example, are there places where other people would make really bad predictions about your actions? your preferences?
- Who is your best next-token predictor?
- Give me some good advice
- Whatâs some good advice youâve received?
- Do you have any really good systems?
- How do you avoid freaking out about scary things?
- What is fun worth?
- What are the best emotions? The worst?
- What would you do if I gave you 20 dollars and you had to spend it today?
- What do you think are some big societal problems?
- Who are some of the best people you know, in terms of:
- altruism
- health
- habits
- giving advice
- being nice to be around
- Is doing good likely to lead to happiness?
- What is a fun tradition that you have, or want to create (with yourself, or with a friend)?
- Who looks up to you?
- What is a dream youâve let go of?
- Are you lying to yourself about anything?
- What lesson took you the longest to unlearn?
- What is something you wouldnât want to change about yourself?
- What question are you trying to answer most in your life right now?
- In what areas are you currently trying to improve?
- What do you value in friendships? What are the best ways they add to your life?